Abstract:
A new superbase-driven self-organization of four molecules of acetylene with one molecule of arylamine to 1-aryl-3ethyl-4-vinylpyrroles in the KOBut/DMSO system has been discovered. The process includes four acts of nucleophilic addition to acetylene followed by intramolecular cyclization of intermediate N,N-bis(1,3-dienyl)-N-arylamine.
Citation:
E. Yu. Schmidt, N. V. Semenova, E. V. Ivanova, I. A. Ushakov, B. A. Trofimov, “Multimolecular self-organization of acetylene and arylamines into 1-aryl-3-ethyl-4-vinylpyrroles in the KOBut/DMSO system”, Mendeleev Commun., 30:3 (2020), 315–317
Linking options:
https://www.mathnet.ru/eng/mendc1182
https://www.mathnet.ru/eng/mendc/v30/i3/p315
This publication is cited in the following 11 articles:
Vladimir B. Orel, Nikita V. Teplyashin, Anastasia A. Manzhueva, Alexander S. Bobkov, “Comparison of Ethynylation Mechanisms of Ketones with Acetylenes in the Presence of Organic t‐Bu‐P4/DMSO and Inorganic KOH/DMSO Superbases: A Detailed Quantum Chemistry Study”, ChemistrySelect, 10:8 (2025)
E. Yu. Schmidt, B. A. Trofimov, “Reaction of acetylenic carbanions with C=N bond: dynamics of development, synthetic divergence, environmental safety”, Russian Chem. Reviews, 93:10 (2024), RCR5145
Damir Z. Absalyamov, Nadezhda M. Vitkovskaya, Vladimir B. Orel, Elena Yu. Schmidt, Boris A. Trofimov, “Quantum‐Chemical Insight into Self‐Organization of Complex Molecules from Acetylene and Anilines Catalyzed by Superbase KOH/DMSO: One‐Pot Cascade Assembly of 1,3‐Bis(arylamines)”, Asian J Org Chem, 12:4 (2023)
Vladimir B. Orel, Andrey A. Zubarev, Ivan A. Bidusenko, Igor A. Ushakov, Nadezhda M. Vitkovskaya, “Quantum-Chemical Study of the Assembly Mechanism of 1-Pyrrolines from N-Benzylaldimines and Arylacetylenes in KOtBu/DMSO Superbasic Medium”, J. Org. Chem., 88:11 (2023), 7058
N. V. Semenova, E. Yu. Schmidt, I. A. Ushakov, B. A. Trofimov, “Acetylene-driven multi-molecular assemblies of high complexity: imidazo[1,2-a]pyridines and 5-chloro-N-[2-(imidazo[1,2-a]pyridin-6-yl)vinyl]pyridin-2-amine”, Mendeleev Commun., 33:2 (2023), 164–166
E. Yu. Schmidt, B. A. Trofimov, “Acetylene in Organic Synthesis. From the Chaos of Small Molecules to Highly Organized Structures. A Review”, Dokl Chem, 505:1 (2022), 127
Ivan V. Saliy, Maxim D. Gotsko, Lyubov' N. Sobenina, Igor A. Ushakov, Boris A. Trofimov, “Chemo- and stereoselective synthesis of E-2-(2-acyl-1-tosylvinyl)pyrroles from tosylmethyl isocyanide (TosMIC) and 2-(acylethynyl)pyrroles”, Tetrahedron Letters, 84 (2021), 153432
Elena Yu. Schmidt, Nadezhda V. Semenova, Igor A. Ushakov, Alexander V. Vashchenko, Boris A. Trofimov, “Multimolecular Self-Organization of 1-Acetyl-1,3-bis(haloarylamines) in KOH/DMSO System: From Acetylene Gas and o-Halo Arylamines toward a Higher Molecular Complexity and Diversity”, Org. Lett., 23:12 (2021), 4743
Najmedin Azizi, Fatemeh Heidarzadeh, Fezeh Farzaneh, “Facile fabrication of porous magnetic covalent organic frameworks as robust platform for multicomponent reaction”, Applied Organom Chemis, 35:11 (2021)
Nadezhda M. Vitkovskaya, Vladimir B. Orel, Damir Z. Absalyamov, Boris A. Trofimov, “Self-Assembly of N-Phenyl-2,5-dimethylpyrrole from Acetylene and Aniline in KOH/DMSO and KOBut/DMSO Superbase Systems: A Quantum-Chemical Insight”, J. Org. Chem., 85:16 (2020), 10617
L. A. Oparina, N. A. Kolyvanov, N. K. Gusarova, B. A. Trofimov, “Chemoselective vinylation of aminophenols with acetylene catalyzed by sodium aminophenolates in aqueous DMSO”, Mendeleev Commun., 30:6 (2020), 788–790
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